Methyl iodide → N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)-N-methylmethanesulfonamide

HRID 2042234Notes

Reaction equation

HRID 2042234 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1.[H-].[Na+].I[CH3:25]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([N:17]([CH3:25])[S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86673215N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

Product 1

HCID 86673223N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)-N-methylmethanesulfonamideYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (200 mg, 0.59 mmol) was dissolved in N,N-dimethylformamide (2.5 mL) and sodium hydride (36 mg, 0.89 mmol) was slowly added at 0° C. 10 minutes later, after adding iodomethane (100 mg, 0.71 mmol), the reaction mixture was stirred for an hour, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered, and then concentrated. The target compound (195 mg, 94% yield) was obtained without purification.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-add77f7933aa42748f506f8b176838c0
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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